Benzoyl Peroxide → 7-(bromomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one

HRID 1988185Notes

Reaction equation

HRID 1988185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[O:11][C:10](=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][C:10](=[O:19])[O:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 577292464-(4-fluorophenyl)-7-methyl-2H-chromen-2-one

Product 1

HCID 194269637-(bromomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-(4-fluorophenyl)-7-methyl-2H-chromen-2-one (24.0, 94.3 mmol), NBS (18.5 g, 103.8 mmol) and benzoyl peroxide (1.14 g, 4.72 mmol) in 470 mL of CCl4 was brought to reflux. The solution was left overnight at reflux and then filtered hot. Once cooled to rt the solvent was removed, the compound was dissolved in CH2Cl2 and a purification was done with a small pad of silica gel using hexane-EtOAc (8/2) to (1/1). The solvent was removed and the solid triturated with hexane-EtOAc and filtered to give the title compound. The remaining solvent was removed to give additional compound contaminated with some starting material and dibromo compound. 1H NMR (400 MHz, acetone-d6): δ 7.67 (2H, m), 7.55 (1H, s), 7.50 (1H, d), 7.40 (3H, m), 6.40 (1H, s) and 4.75 (2H, s).

Workup

  1. temperatureto reflux
  2. temperatureat reflux
  3. filtrationfiltered hot
  4. customwas removed
  5. dissolutionthe compound was dissolved in CH2Cl2
  6. customa purification
  7. customThe solvent was removed
  8. customthe solid triturated with hexane-EtOAc
  9. filtrationfiltered

Sources & evidence

ORD record
ord-286febfb7e924532958035e060139d3c
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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